Methanesulfonamide → N-(2-{3-[4-(4-chloro-phenyl)-piperazin-1-yl]-phenyl}-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carbonyl)-methanesulfonamide

HRID 2045356ノート

反応式

HRID 2045356 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:15]=[C:16]([CH:20]4[C:29]([CH3:31])([CH3:30])[CH2:28][C:27]5[C:22](=[CH:23][CH:24]=[C:25]([C:32](O)=[O:33])[CH:26]=5)[NH:21]4)[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:35][S:36]([NH2:39])(=[O:38])=[O:37]>CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14]3[CH:15]=[C:16]([CH:20]4[C:29]([CH3:30])([CH3:31])[CH2:28][C:27]5[C:22](=[CH:23][CH:24]=[C:25]([C:32]([NH:39][S:36]([CH3:35])(=[O:38])=[O:37])=[O:33])[CH:26]=5)[NH:21]4)[CH:17]=[CH:18][CH:19]=3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 72879MethanesulfonamideHCID 584762472-{3-[4-(4-Chloro-phenyl)-piperazin-1-yl]-phenyl}-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid

生成物 1

HCID 53491975N-(2-{3-[4-(4-chloro-phenyl)-piperazin-1-yl]-phenyl}-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carbonyl)-methanesulfonamide収率 26%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 2-{3-[4-(4-chloro-phenyl)-piperazin-1-yl]-phenyl}-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (100 mg, 0.21 mmol), 1-3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (60.5 mg, 0.32 mmol), 4-dimethylaminopyridine (39 mg, 0.32 mmol), methane sulfonamide (60 mg, 0.63 mmol) in dichloromethane (10 mL) was refluxed for 12 hours. Removal of the solvent afforded an oil residue. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water) afforded N-(2-{3-[4-(4-chloro-phenyl)-piperazin-1-yl]-phenyl}-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carbonyl)-methanesulfonamide (30 mg, 26%) as a light yellow solid: LC/MS m/e calcd for C29H33ClN4O3S M+: 553.13, observed: 553.2.

後処理

  1. temperaturewas refluxed for 12 hours
  2. customRemoval of the solvent
  3. customafforded an oil residue
  4. customPurification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water)

出典と根拠

ORDレコード
ord-aa27c5e4df43471d92ba2967efc697f4
出典データセット
uspto-grants-2013_11
特許番号
US08586747B2

反応ノート

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